| 3. Round | 03/11/1888 | Everton FC | - | Bolton Wanderers | 2:1 | ||||
| 3. Round | 05/11/1888 | West Bromwich Albion | - | Bolton Wanderers | 1:5 | ||||
| 3. Round | 17/11/1888 | Bolton Wanderers | - | West Bromwich Albion | 1:2 | ||||
| 3. Round | 24/11/1888 | Bolton Wanderers | - | Preston North End | 2:5 | ||||
| 4. Round | 08/12/1888 | Blackburn Rovers | - | Bolton Wanderers | 4:4 |  |
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| 4. Round | 22/12/1888 | Bolton Wanderers | - | Accrington FC | 4:1 | ||||
| 4. Round | 26/12/1888 | Derby County | - | Bolton Wanderers | 2:3 | ||||
| 4. Round | 29/12/1888 | Bolton Wanderers | - | Wolverhampton Wanderers | 2:1 | ||||
| 5. Round | 12/01/1889 | Aston Villa | - | Bolton Wanderers | 6:2 |
England